The effect of different amine bases in the Swern oxidation of β-amino alcohols

Tetrahedron Letters

Volumn 38, Issue 12, 1997, Pages 2053-2056

  Chrisman, William ^a   Singaram, Bakthan ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; CARBONYL DERIVATIVE; TERTIARY AMINE;

ARTICLE; CHEMICAL REACTION; OXIDATION; PROTECTION; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

EID: 0031585107     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00283-9     Document Type: Article

References (23)

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2. b) Beaulieu, P. L.; Wernic, D. ibid 1996, 61, 3635;
3. c) Dondoni, A.; Perone, D.; Merino, P. ibid 1995, 60, 8074.
4. 2. Pace, R. C.; Kabalka, G.W. J. Org. Chem. 1995, 60, 4838, and references therein.
5. 3. a) Beardley, D.A.; Fisher, G.B.; Goralski, C.T.; Nicholson L.W. ; Singaram, B. Tetrahedron Lett. 1994, 35, 1511;
6. b) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629;
7. c) Abdel-Magid, A.F., Editor. ACS Symposium Series #641, (1996) Reductions in Organic Sythesis ; Recent Advances and Practical Applications, Washington D.C., American Chemical Society.
8. 4. Lyle, R.E; Maloney, J.R.; White, R.J. Org. Prep. and Proced. 1980, 12, 255.
9. 5. a) Fenselau, A.H.; Moffatt, J. G. J. Am Chem. Soc. 1966, 1762;
10. b) Omura, K.; Swern, D., Tetrahedron 1978, 34, 1651;
11. c) Epstein, W.W.; Sweat, F.A. Chemical Reviews (American Chem. Soc.) 1967, 67, 247.
12. 6. a) Ina, H.; Ito, M.; Kibayashi, C. J. Org. Chem. 1996, 61, 1023;
13. b) Corey, E.J.; Chen, C.P.; Reichard, G.A. Ibid 1989, 30, 5547;
14. c) Krysan, D.J.; Haight, A.R.; Lallaman, J.E.; Langridge, D.C.; Menzia, J.A.; Narayanan, B.A.; Pariza, R.J.; Reno, D.S.; Rockway, T.W.; Stuk, R.L.; Tien, J.H. Org. Prep. and Proced. 1993, 25, 437.
15. 7. Gmeiner, P.; Kartner, A.; Junge, D. Tetrahedron Lett. 1993, 34, 4325.
16. 8. Samples of pure α-amino ketones to be used as GC standards were obtained by reoxidation of the crude reaction mixture. For example, 1 was Swern oxidized to give 93% of 2 and 5% recovered 1, plus a trace of side products. The crude mixture was reoxidized, and upon short path distillation furnished 99% pure 1-(4-morpholino)-2-cyclohexanone (2).
17. 9. N-benzyl-N-methylethanol-amine was purchased from Aldrich and used as received. β-amino alcohol 5 was prepared by hydroboration of the morpholino enamine of (1R, 5S)-(+)-nopinone. All other β-amino alcohol substrates were prepared by known methods, from commercially available epoxides and amines: Harris, E.; Fisher, B.; Beardsley, D.; Lee, L.; Goralski, C.T.; Nicholson, L.W.; Singaram, B. J. Org. Chem. 1994, 59, 7746.
18. 4) and evaporation of the combined orgainc portions, gave the α-amino ketone and N-ethylpiperidine mixture. The N-ethylpiperidine was evaporated (25 °C, 0.3 Torr), and the crude product was purified by short path distillation to yield 1-(4-morpholino)-2-cyclohexanone as a colorless oil: 0.85g, 92% yield; bp 65 °C (0.3 Torr).
19. 11. Green, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis; Wiley-Interscience: New York, 1991; pp. 327-330.
20. 12. a) Shin, Y.; Chun, K.H.; Shin, J.; Aspinall, G.O. Bull. Korean Chem. Soc. 1995, 16, 625.
21. b) Krysan, D.J. etal Org. Prep. and Proced. Int. 1993, 25, 437.
22. 13. Singaram, B.; Goralski, C.T. Unpublished results, University of California at Santa Cruz.
23. 14. Brown, H.C.; Kramer, G.W.; Levy, A.B.; Midland, M.M. Organic Synthesis via Boranes; Wiley-Interscience: New York, 1975; pp. 191-211.